Even if you can only name a handful of rappers, Drake is probably one of them. Not so many years ago, he was among the planet’s biggest celebrities, named in the same breath as Taylor Swift and Beyoncé and breaking chart records set by the Beatles. Many of his dozens of hit singles – Work, One Dance, Hotline Bling and God’s Plan – were ubiquitous, among the last truly crossover radio hits.
Drake is still landing chart spots (if not critical acclaim), but now it’s his foray into the “creator economy” that’s raising eyebrows – shilling for a crypto casino, fraternising with manosphere influencers and, just last weekend, live-streaming dates with OnlyFans models. So what’s this all about? Is Toronto’s once-golden boy having a midlife crisis – or is it a media-savvy pivot? Here’s how Drake got caught up in the “creator economy”.
1. He’s live-streaming his ‘dates’
On Saturday, Drake appeared as the eligible bachelor on a speed-dating show on the live-streaming platform Kick, the online home to many controversial internet celebrities such as the “looksmaxxer” Clavicular. Though the “20-v-1 challenge” is an established format (named for the women-to-men ratio), Drake is by far the biggest name to have ever taken part. This particular broadcast played out like a Bad Place Blind Dates, over three desultory hours. Twenty women, mostly performers on the adult platform OnlyFans, competed for Drake’s affections along with cash prizes, holidays and Hermès bags in bawdy challenges such as “Wife, Pipe, Bestie”. (You may know it as “Kiss, Marry, Kill”.) Among them was Lily Phillips, the Briton notorious for a 2024 stunt in which she attempted to have sex with 100 men in 24 hours. The chosen lucky lady was a cosplay creator and “goth baddie” named Pinkchyu, who requested, as her prize, that Drake buy her mother a house and also bark like a dog. He agreed to both. Complex reported he was “like a poodle”. Rest easy, Cilla Black: you were not cut out for this world.
2. He’s partnered with a gambling company
Drake’s participation came as part of a broader partnership with Australian crypto-gambling platform Stake, which backs Kick. According to the Financial Times, Drake was an early adopter of the platform, betting with bitcoin, and became a brand ambassador in 2022, in a deal reportedly worth $100m a year. Now the rapper drives traffic by live-streaming himself gambling, giving away money and performing social-media-friendly stunts. Last year, a video of Drake apparently being bothered by a drone at his Sydney penthouse went viral before many users clocked that it was a staged ad. Last month, a video was “clipped” from a stream, showing Drake saying “Oh my God” 70 times after a big win. Drake’s golden deal with the gambling company has drawn scrutiny: an investigation by Bloomberg Businessweek found that the rapper saw four times as much success playing Stake’s slot machines as the average person (according to Bloomberg’s methodology, which is disputed by Stake). He’s also been accused in a class action lawsuit of using the platform to inflate streams of his songs, although a federal judge has paused the lawsuit, stating the plaintiffs must first complete arbitration.
3. Finally, he has some new friends
Drake is still making music, and even swamping the charts, having put out three albums back in May – but his priorities have been shifting for a while. In 2023, he rapped: “My youngins richer than you rappers and they all stream.” Lately he’s been running with the new-gen influencers Adin Ross and Kai Cenat, twentysomethings with millions of followers. Drake has even been trying to ingratiate himself with the next new gen, delivering an (prerecorded) address and free merch to Cenat’s Streamer University bootcamp last month.
4. … but is he on his worst behaviour?
Drake has always been corny, cringe and perhaps too comfortable with self-deprecation. Now, some say his flirtations with content are bringing out the worst of those tendencies, shifting his public persona and potentially tarnishing his legacy. In GQ, Josiah Gogarty noted that Drake’s fraternising with streamers has him increasingly skirting the online manosphere, noting that the speed-dating “meat market” was also hosted by Kyle Forgeard, from the Trump-supporting Nelk Boys gang of YouTubers. Drake himself can seem to provoke people online, Gogarty argued, pointing to his “whiny, almost incel-coded” posts, such as an Instagram list of “reasons why I’m single … I care too deeply.” Having previously penned a “joyful women’s-empowerment anthem” (per the New Yorker!) in Nice For What, and declared himself a Certified Lover Boy, Drake’s latest hit is called Janice, STFU. By way of apology, in June, he threw some “Janice-only parties”, with government ID a requirement of entry. As Gogarty wondered: “Is Drake a better rage baiter than rapper now?”
5. He will soon turn 40
Some have drawn a link between Drake’s recent activities – participating in online “challenges”, hanging out with twentysomethings, gambling, gaming and degrading himself in front of young women – with his looming milestone birthday. Vulture declared of the live-dating stream: “This is Drake’s midlife crisis.” The past few years have not been kind to October’s Very Own (setting aside its co-founder’s vast fame and fortune, of course). The last time Drake was central to the cultural conversation was early 2024, and his highly public feud with Kendrick Lamar. Lamar was not only widely deemed the victor with his record-breaking, Grammy-winning diss track Not Like Us – but took his victory lap at the Super Bowl, leading seemingly the entire stadium in a rap that accuses Drake of being a paedophile. To be very clear, Drake has denied this.
6. Grimly, he might be ahead of the game
Those of us who had time for the old Drake might be bewildered by his evolution, if not already long checked out. But he’s likely being driven by the changing cultural tides. The monoculture by which he became a household name is mostly gone, receding in memory with millennials’ youth, while younger audiences don’t draw the same distinctions between streamers and celebrities, or social-media stunts and “authentic” entertainment. Just as you may know someone valiantly experimenting with the front-facing camera on Instagram, traditional stars not yet close to retirement are feeling the pressure to adapt. (See Timothée Chalamet’s #sponcon for the prediction market Kalshi.) Drake’s pivot to influencer mode is arguably one of his most savvy, investing his celebrity in growing economies and platforms seeking mainstream respectability, and reinventing himself with younger generations. Rather than going through a midlife crisis, Drake may be once again ahead of the curve.